{(4R,5R)-5-[(S)-1-(benzyloxy)propan-2-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}methyl-4-methylbenzenesulfonate

Base Information

Chemical Name:{(4R,5R)-5-[(S)-1-(benzyloxy)propan-2-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}methyl-4-methylbenzenesulfonate
CAS No.:1621332-18-0
Molecular Formula:C₂₃H₃₀O₆S
Molecular Weight:434.554
Hs Code.:

Synonyms:{(4R,5R)-5-[(S)-1-(benzyloxy)propan-2-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}methyl-4-methylbenzenesulfonate

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Chemical Property of {(4R,5R)-5-[(S)-1-(benzyloxy)propan-2-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}methyl-4-methylbenzenesulfonate

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Technology Process of {(4R,5R)-5-[(S)-1-(benzyloxy)propan-2-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}methyl-4-methylbenzenesulfonate

There total 7 articles about {(4R,5R)-5-[(S)-1-(benzyloxy)propan-2-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}methyl-4-methylbenzenesulfonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

: 1621332-17-9
{(4R,5R)-5-[(S)-1-(benzyloxy)propan-2-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol

: 98-59-9
p-toluenesulfonyl chloride

: 1621332-18-0
{(4R,5R)-5-[(S)-1-(benzyloxy)propan-2-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}methyl-4-methylbenzenesulfonate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 1h;
DOI:10.1002/ejoc.201402235

Reference yield:

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 1621332-18-0
{(4R,5R)-5-[(S)-1-(benzyloxy)propan-2-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}methyl-4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 7 steps

1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 1 h / 0 - 20 °C

2: diisobutylaluminium hydride / toluene; dichloromethane / 0.25 h / -78 °C

3: benzene / 1 h / 80 °C

4: AD-mix β; methanesulfonamide / tert-butyl alcohol; water / 6 h / 0 °C

5: toluene-4-sulfonic acid / acetone / 12 h / 20 °C

6: diisobutylaluminium hydride / toluene; dichloromethane / 1 h / 0 - 20 °C

7: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C

With dmap; methanesulfonamide; trifluorormethanesulfonic acid; AD-mix β; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; In dichloromethane; cyclohexane; water; acetone; toluene; tert-butyl alcohol; benzene; 3: |Wittig Olefination / 4: |Sharpless Dihydroxylation;
DOI:10.1002/ejoc.201402235

Reference yield:

: 81470-73-7
ethyl (4R,2E)-5-(benzyloxy)-4-methylpent-2-enoate

: 1621332-18-0
{(4R,5R)-5-[(S)-1-(benzyloxy)propan-2-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}methyl-4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 4 steps

1: AD-mix β; methanesulfonamide / tert-butyl alcohol; water / 6 h / 0 °C

2: toluene-4-sulfonic acid / acetone / 12 h / 20 °C

3: diisobutylaluminium hydride / toluene; dichloromethane / 1 h / 0 - 20 °C

4: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C

With dmap; methanesulfonamide; AD-mix β; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; In dichloromethane; water; acetone; toluene; tert-butyl alcohol; 1: |Sharpless Dihydroxylation;
DOI:10.1002/ejoc.201402235